January 26, 2024

262: 🪜Climbing Down the Entrepreneurial Ladder — Rolling in D🤦🏻‍♀️h

14 minutes

“Things today are waaayyyyy better than Things have ever been. Cavemen had sticks. In the Middle ages they had typhoid. We have iPhones and Hermann Miller chairs and shoes with air in the soles. Inside the soles! How do they get the air inside the soles??? We are living in the Golden Age of Things, in the Golden Empire of Things.”

—Shalom Auslander's Fetal Position via Beckett Drove a Deux Chevaux

I first encountered the Apple billboard a few days after Christmas. I was walking down Fourteenth Street in the Meatpacking district, and there it was—an Apple ad declaring “Newphoria!” in enormous print.

We don’t need newphoria. We need oldphoria, the joy in what already exists. We need simplephoria, the joy in streamlining. We need enoughphoria, the celebration that what we have and who we are is already enough. Newphoria, at least as it relates to running a small business, is not always all it’s cracked up to be.

Today’s post is a crossover from Rolling in D🤦🏻‍♀️h—you can read the post and reply in the comments here: Climbing Down the Entrepreneurial Ladder.

📝 Permission

Celebrate your own -phoria, the joy in running your business in the way that works best for you!

🔗 Resources Mentioned

D🤦🏻‍♀️h Articles: Love That! For You 🙄, COnTenT cReaToRs exist and subsist in the verrrrrrry looooooooooooong tail’s trough, 🤬 Rant From the Wound: Why This Platitude Meme Engraged Me, Serendipity signage

Katherine Raz on closing the second location of her Fernseed business in Tacoma

Emily McDowell’s experience of running a small business that blew up—in a good way—but also led to burnout: The truth about going mega-viral, part one and part two.

Nathan Barry’s The Ladders of Wealth Creation

Jonathan Field’s The Unfortunate Middle

JB for CNBC: Treat your career like a smart phone, not a ladder

NYT: Climbing Down the Corporate Ladder. Big thanks to Rob Walker for including me in this Workologist column! It’s still a career highlight. He’s now here on Substack at The Art of Noticing

Video: If you want to geek out further on idea gathering process: here’s a Loom walkthrough of my Collection Bucket in Notion.

Recent Free Time workshop by Stephanie Huston with a template for creating and batching content for the year ahead.

Apps: Substack

📚 Books Mentioned

I’m not immune from status-chasing—none of us are. In his book, The Status Game, Will Storr categorizes these games into three types: dominance, success, and virtue. My two all-time favorite books on this topic are Alain de Botton’s Status Anxiety and Wanting by Luke Burgis who is on Substack at Ride or Drive and Anti-Mimetic.

Free Time: Lose the Busywork, Love Your Business

Pivot: The Only Move That Matters Is Your Next One

Life After College

🎧 Related Episodes

Listen to the audio version of Jonathan Fields reading “The Unfortunate Middle” here, and check out our series of 12 SPARKED episodes (Spotify Playlist).

Pivot: 305: Is What You’re Wanting Actually What’s Best For You? With Luke Burgis

Pivot x RadReads conversations on status with Khe Hy (Spotify Playlist)

Free Time: Here are some of my favorite Free Time conversations with small business owners who downsized their operations:

016: IP Licensing and “No Full-Time Employees” with Lee LeFever

131: Scaling Joy While Streamlining Business Overhead with Kaneisha Grayson

157: Downshifting to a Delightfully Part-Team Team with Laura Roeder

173: Cut Your Losses—Even While Pivoting in Public with Khe Hy

205: Turning Down a $200K Two-Book Traditional Publishing Deal with Paul Millerd

241: Finding Freedom and Financial Reciprocity through a Paid Newsletter

📝 Check out full show notes and share with friends: https://itsfreetime.com/episodes/262

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By Jenny Blake

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